3-Bromoquinolin-6-amine → 3-Methoxyquinolin-6-amine

HRID 2279404Notes

Reaction equation

HRID 2279404 reaction equation
Br[C:2]1[CH:3]=[N:4][C:5]2[C:10]([CH:11]=1)=[CH:9][C:8]([NH2:12])=[CH:7][CH:6]=2.[CH3:13][O-:14].[Na+]>CO.[Cu]>[CH3:13][O:14][C:2]1[CH:3]=[N:4][C:5]2[C:10]([CH:11]=1)=[CH:9][C:8]([NH2:12])=[CH:7][CH:6]=2

Participants

5

Reactant 2

HCID 52002663-Bromoquinolin-6-amineHCID 10942334Sodium Methoxide

Product 1

HCID 534257963-Methoxyquinolin-6-amineYield 59.8%

Reagents, catalysts & solvents 2

HCID 23978CopperCatalystHCID 887MethanolSolvent

Conditions

Temperature
135 °C

Procedure

A suspension of 3-bromo-quinolin-6-ylamine (9.0 g, 40.3 mmol, 1.0 eq), sodium methoxide (10.9 g, 201.7 mmol, 5.0 eq) and copper powder (7.7 g, 121.0 mmol, 3.0 eq) in methanol (240 mL) is heated at 135° C. for 15 hours. The reaction mixture is then filtered and the filtrate is concentrated to give a yellow residue that is purified by column chromatography (silica gel, eluent: petroleum ether:ethyl acetate:triethylamine, 2:1:0.05, v/v/v) to afford 3-methoxy-quinolin-6-ylamine as a yellow solid (4.2 g, 59% yield).

Workup

  1. filtrationThe reaction mixture is then filtered
  2. concentrationthe filtrate is concentrated
  3. customto give a yellow residue that
  4. customis purified by column chromatography (silica gel, eluent: petroleum ether:ethyl acetate:triethylamine, 2:1:0.05, v/v/v)

Sources & evidence

ORD record
ord-31e7d9fa57f844548ee407eab79e7b38
Source dataset
uspto-grants-2015_09
Patent number
US09133219B2

Reaction notes

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